Stratejoy Essay Contest – Finalist #11 – Jennifer Winter

*This post is an entry in the 1st Annual Stratejoy Essay Contest. Each day throughout the month of February, we will be featuring one of the 20 finalists writing their answer to the question: How do you live life on your own terms? On February 29th, we will open the voting to YOU, our community, to select the winner of the $500 prize.*

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I sat on the edge of my bed and surveyed my handiwork. Somehow, I’d managed to pack an entire month’s worth of necessities into my sturdy camping pack. The first time I’d used this pack was for my first trip overseas with my ex boyfriend, and every trip for the next eight years after. Now, several months after that relationship had ended, I was venturing out without him. I shuddered at the thought – immediately angry at myself for feeling so dependent on him to do something I truly loved, and devastated at the idea I’d be exploring someplace new without my best friend.

To me, this trip was the perfect remedy. Traveling for a month in Thailand on my own would be difficult emotionally, yet I saw no other way to get myself back on track. I had ended my relationship specifically because I no longer knew who I was. Somehow, while falling in love I’d lost sight of who I was, and eight years later I was a mere shadow of my former self.

My friends and family, however, had wildly differing opinions on how best to mend a broken heart. Suggestions ranged from online dating, to cooking classes to adopting a puppy. But when I mentioned I would be spending a month in Thailand, they smiled brightly and immediately asked who I’d be going with. Their smiles faded when I revealed I was going solo, many proceeding to attempt to talk me out of it.

I patiently listened, promised to be careful and vowed to do my best to email often, then promptly booked my flights. There was no talking me out of this – I was determined to go. I knew I needed this, even if everyone else thought I was impulsive or running away. A knock at my front door snapped me out of my trance. My ride to the airport – it was time. I slung my pack over my shoulder and headed for the door – completely unprepared for the adventure ahead.

Many hours later, I was happily sipping Udon and drinking beer in a Tokyo airport bar. Everything around me was strange and wonderful. The unfamiliarity of the setting was oddly comforting – which was my first hint I knew myself better than I thought.

This trip would not only enable me the time and distance I needed to start to heal, but would force me to handle everything on my own. No friends to call, no family nearby and no boyfriend to share the experience. I was completely alone.

Determined to test my travel instincts, I made a promise to myself I wouldn’t over- plan. I would make reservations only when absolutely necessary, and I would decide what to do each day over breakfast. After years of taking cues from others, I had to know if I had a mind of my own.

My first morning in Bangkok was awkward reassurance that I was in fact, my own person. I had sequestered myself to a quiet corner, sipping my coffee, occasionally nibbling on a bowl of fresh fruit.

Despite my sensitivity to being tagged as a tourist (as if my appearance wasn’t enough) I pulled out a guidebook for inspiration on the day’s activities. As I
suspected, none of the suggested itineraries inspired me, and I resolved to just wander the streets of this massive city, and hope I wouldn’t get lost (I couldn’t read the street signs so maps were somewhat useless). I finished my coffee, tucked away my guidebook and never opened it again.

The next few weeks were filled with wonder, stress, anxiety, loneliness and seemingly endless beauty. Every decision was made based on exactly what I wanted and nothing else.

I knew friends and family would ask about the elephants when I returned, but I didn’t feel compelled to see them. I spent weeks traipsing all over Thailand and never saw a single elephant.

Except for the ones on my beer bottles, and that’s just the way I wanted it.

She translates her 14 years of corporate combat experience to help young women navigate their careers through her column for The Daily Muse, and shares her own experiences tackling her fears on her blog FearLess Jenn.

*This post is an entry in the 1st Annual Stratejoy Essay Contest. Each day throughout the month of February, we will be featuring one of the 20 finalists writing their answer to the question: How do you live life on your own terms? On February 29th, we will open the voting to YOU, our community, to select the winner of the $500 prize.*